The naphthyridine compound, cas is 72754-05-3 name is 6-Bromo-1,8-naphthyridin-2-ol, mainly used in chemical industry, its synthesis route is as follows.
72754-05-3, c) (EVtert-butyl 3-(7-oxo-7.8-dihvdro-l ,,8-naphtfayridin-3-yr)acrylate; A reaction vessel was charged with 6-bromo-l,8-naphthyridin-2(lH)-one (1.5g, 6.69 mmol), tert-bxyl acrylate (4.86 mL, 33.45 mmol), and (J-Pr)2EtN (3.5 niL, 20.07 mmol) followed by DMF (40 mL). The solution was de-oxygenated with argon for 20 min. The mixture was treated with Pd(OAc)2 (150 mg, 0.67 mmol) and P(o-tol)3 (407 mg, 1.34 mmol) then heated to 100 0C for 15 h (overnight). A TLC anlaysis indicated that only the starting arylhalide is present. At this time the mixture was a yellow suspension. To this mixture was added 20 DMSO (20 mL) and an additional 75 mg OfPd(OAc)2. The mixture was heated at 100 0C for 24 h. After cooling, the dark mixture was filtered through celite and the filter cake was rinsed with EtOAc (100 mL). The filtrate was extracted with EtOAc (2 x 100 mL). The combined organic fractions were washed with brine (2 x 100 mL), H2O (100 mL), dried over MgSO4 and filtered through a pad of silica gel. The filtrate was concentrated to about 50 mL then treated with about 150 mL hexanes to form a precipitate. The precipitate was filtered to give the product as a light brown solid. Yield: 700 mg(39%); 1H-NMR (300 MHz, DMSO-d6) delta 12.36 (s, IH), 8.83 (d, IH, J = 2.3 Hz), 8.53 (d, IH, J = 2.3 Hz), 7.89 (d, IH, J = 9.0 Hz), 7.64 (d, IH, J = 18.0 Hz), 6.65 (d, IH, J = 18.0 Hz), 6.62 (m, IH)5 1.51 (s, 9H); ESIMS m/z 273 [Ci5H16N2O3 + H]+
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Reference£º
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem